This invention relates to novel N-(heterocyclicaminocarbonyl)-o-alkenylbenzenesulfonamides which are useful as agricultural chemicals and in particular as herbicides and growth regulants.
Netherlands Patent No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (I) and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Z is methyl or methoxy; or their agriculturally suitable salts; provided that: PA1 n is 0 or 1; PA1 R.sub.1 is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.4 alkyl, OCF.sub.3 or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.5 and R.sub.6 are independently H or CH.sub.3 ; PA1 A is ##STR7## X is H, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.3 or Cl; PA1 Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 Z is N, CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA1 Y.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl; PA1 X.sub.2 and Y.sub.2 are independently CH.sub.3 or OCH.sub.3 ; and PA1 Q is O or CH.sub.2 ; PA1 (1) Compounds of Formula I wherein R.sub.1 is H; PA1 (2) Compounds of Preferred (1) wherein A is ##STR8## and Z is N or CH; (3) Compounds of Preferred (2) wherein R.sub.5 and R.sub.6 are H; and PA1 (4) Compounds of Preferred (3) wherein X is CH.sub.3, OCH.sub.3 OCH.sub.2 CH.sub.3 or CH.sub.2 OCH.sub.3, and Y is CH.sub.3 or OCH.sub.3. PA1 n is 0 or 1; PA1 R.sub.1 is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.4 alkyl, OCF.sub.3 or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.5 and R.sub.6 are independently H or CH.sub.3 ; and PA1 Z is N or CH. PA1 (a) The compound of Formula II can be suspended or dissolved in an alkanol solvent in the presence of at least two equivalents of alkoxide. The alkoxide can be added directly as alkali metal or alkaline earth metal alkoxide or can be generated by the addition to the alkanol solvent of at least two equivalents of a base capable of generating alkoxide from the solvent. Suitable bases include, but are not limited to, the alkali and alkaline earth metals, their hydrides and tert-butoxides. For example, when X' is methoxy, the compound of Formula II could be suspended or dissolved in methanol in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents of sodium hydride could be used in place of the sodium methoxide. PA1 (b) The compound of Formula II can be suspended or dissolved in an inert solvent in the presence of at least two equivalents of alkoxide. Suitable inert solvents include, but are not limited to, acetonitrile, THF and dimethylformamide. The alkoxide may be added directly as alkali metal or alkaline earth metal alkoxide or may be generated from alkanol and a base as described in (a) above. For example, when X' is methoxy, the compound of Formula II could be suspended or dissolved in THF in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents each of methanol and sodium hydride could be used instead of sodium methoxide.
Compounds of Formula (II), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974): ##STR2## wherein R is pyridyl.
In U.S. Pat. No. 4,127,405, compounds are disclosed of the general formula: ##STR3## wherein R.sub.1 is ##STR4## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA2 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA2 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA2 (1) when Z is other than N or CH, then X is H, CH.sub.3 or OCH.sub.3 and Y is CH.sub.3 or OCH.sub.3 ; and PA2 (2) when Z is N and X is Cl, then Y is CH.sub.3.
In particular, the patent discloses orthosubstituted compounds wherein the substitution is C.sub.1 -C.sub.4 alkyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly known as herbicides. The need exists however, for still more effective herbicides especially those which destroy or retard weeds without causing significant damage to useful crops.